Iron(III)-catalysed nitration of non-activated and moderately activated arenes with nitrogen dioxide-molecular oxygen under neutral conditions

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 19, 1996, Pages 2385-2389

  Suzuki, Hitomi ^a   Yonezawa, Shuji ^a   Nonoyama, Nobuaki ^a   Mori, Tadashi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748916442     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960002385     Document Type: Article

References (32)

1. B. Milligan, J. Org. Chem., 1983, 48, 1495;
2. J. D. S. Goulden and D. J. Millen, J. Chem. Soc., 1950, 2620;
3. A. I. Titov, Zh. Obshch. Khim., 1937, 7, 591;
4. A. I. Titov and A. N. Baryshnikova, Zh. Obshch. Khim., 1936, 6, 1801;
5. J. A. Pinck, J. Am. Chem. Soc., 1927, 49, 2536.
6. G. A. Olah, R. Malhotra and S. C. Narang, J. Org. Chem., 1978, 43, 4628;
7. G. B. Bachman and C. M. Vogt, J. Am. Chem. Soc., 1958, 80, 2987;
8. A. Schaarschmidt, H. Balzerkiewicz and J. Gante, Ber. Dtsch. Chem. Ges., 1925, 58, 499;
9. A. Schaarschmidt, Ber. Dtsch. Chem. Ges., 1924, 57, 2065.
10. E. Bosch and J. K. Kochi, J. Org. Chem., 1994, 59, 3314.
11. See: A. I. Titov, Tetrahedron, 1963, 19, 557.
12. For a general survey, see: T. Mori and H. Suzuki, Synlett, 1995, 383.
13. H. Suzuki and T. Mori, J. Chem. Soc., Perkin Trans. 2, 1995, 41.
14. For a general survey of aromatic nitration, see: G. A. Olah, R. Malhotra and S. C. Narang, Nitration, Methods and Mechanisms, VCH, New York, 1989;
15. K. Schofield, Aromatic Nitration, Cambridge University Press, London, 1980.
16. H. Suzuki and T. Mori, J. Chem. Soc., Perkin Trans. 2, 1996, 677;
17. L. Eberson and F. Radner, Acta Chem. Scand., 1994, 48, 937.
18. K. Smith, A. Musson and G. A. DeBoos, Chem. Commun., 1996, 469.
19. See, also: L. Delande, P. Laszlo and K. Smith, Acc. Chem. Res., 1993, 26, 607;
20. L. V. Malyshera, E. A. Paukshtis and K. G. Ione, Catal. Rev.-Sci. Eng., 1995, 37, 179.
21. T. B. Bonner, R. A. Hancock, G. Yousif and F. R. Rolle, J. Chem. Soc. B, 1969, 1237;
22. G. R. Underwood, R. S. Silverman and A. Vanderwalde, J. Chem. Soc., Perkin Trans. 2, 1973, 1177.
23. K. H. Meyer and W. E. Eibers, Ber. Dtsch. Chem. Ges., 1921, 54, 337.
24. S. Fukuzumi and J. K. Kochi, J. Am. Chem. Soc., 1981, 103, 7240.
25. L. Bardi, E. Fasani and A. Albini, J. Chem. Soc., Perkin Trans. 1, 1994, 545;
26. P. Maslak and W. H. Chapman, Jr., J. Org. Chem., 1990, 55, 6334.
27. H. Suzuki, T. Murashima and T. Mori, J. Chem. Soc., Chem. Commun., 1994, 1443.
28. C. C. Addison, L. J. Blackwell, B. Harrison, D. H. Jones, N. Logan, E. K. Nunn and S. C. Wallwork, J. Chem. Soc., Chem. Commun., 1973, 347.
29. For a review of metal nitrate-nitrogen dioxide adducts, see: C. C. Addison, Chem. Rev., 1980, 80, 21.
30. L. J. Blackwell, E. K. Nunn and S. C. Wallwork, J. Chem. Soc., Dalton Trans., 1975, 2068.
31. J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz, J. Org. Chem., 1987, 52, 827.
32. C. Djordjević, J. Lewis and R. S. Nyholm, J. Chem. Soc., 1962, 4778.